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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.
Term:N-methylnicotinate
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Accession:CHEBI:18123 term browser browse the term
Definition:An iminium betaine that is the conjugate base of N-methylnicotinic acid, arising from deprotonation of the carboxy group.
Synonyms:exact_synonym: 1-methylpyridinium-3-carboxylate
 related_synonym: 1-Methyl-3-pyridiniumcarboxylate;   1-Methylpyridinio-3-carboxylate;   1-methylnicotinate;   3-Carboxy-1-methylpyridinium hydroxide inner salt;   Betain nicotinate;   Betaine nicotinate;   Caffearin;   Caffearine;   Coffearin;   Formula=C7H7NO2;   Gynesine;   InChI=1S/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3;   InChIKey=WWNNZCOKKKDOPX-UHFFFAOYSA-N;   N-methyl-nicotinate;   Nicotinic acid N-methylbetaine;   SMILES=C[n+]1cccc(c1)C([O-])=O;   Trigenelline;   Trigonellin;   Trigonelline
 alt_id: CHEBI:12522;   CHEBI:19067;   CHEBI:7320
 xref: Beilstein:3905114;   CAS:535-83-1;   HMDB:HMDB0000875;   KEGG:C01004;   KNApSAcK:C00001555
 xref_mesh: MESH:C009560
 xref: MetaCyc:METHYLNICOTINATE;   PMID:13128691;   PMID:17190852;   PMID:185134;   PMID:22242555;   PMID:22312719;   PMID:22393699;   PMID:22559314;   PMID:24047691;   Reaxys:3905114
 cyclic_relationship: is_conjugate_base_of CHEBI:50521


show annotations for term's descendants           Sort by:
N-methylnicotinate term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Ace angiotensin I converting enzyme multiple interactions ISO
EXP		 oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of ACE mRNA]]; oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of ACE protein]]; trigonelline affects the reaction [INS2 protein affects the expression of ACE mRNA]; trigonelline affects the reaction [INS2 protein affects the expression of ACE protein]
oltipraz inhibits the reaction [trigonelline inhibits the reaction [Glucose results in increased expression of ACE mRNA]]; trigonelline inhibits the reaction [Glucose results in increased expression of ACE mRNA]		 CTD PMID:29211853 NCBI chr10:91,410,129...91,430,246
Ensembl chr10:90,910,316...90,931,131 		JBrowse link
G Ace2 angiotensin converting enzyme 2 multiple interactions ISO
EXP		 oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of ACE2 mRNA]]; oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of ACE2 protein]]; trigonelline affects the reaction [INS2 protein affects the expression of ACE2 mRNA]; trigonelline affects the reaction [INS2 protein affects the expression of ACE2 protein]
oltipraz inhibits the reaction [trigonelline inhibits the reaction [Glucose results in decreased expression of ACE2 mRNA]]; trigonelline inhibits the reaction [Glucose results in decreased expression of ACE2 mRNA]		 CTD PMID:29211853 NCBI chr  X:33,925,458...33,972,851
Ensembl chr  X:30,293,589...30,340,977 		JBrowse link
G Agt angiotensinogen multiple interactions ISO
EXP		 oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of AGT mRNA]]; oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of AGT protein]]; trigonelline affects the reaction [INS2 protein affects the expression of AGT mRNA]; trigonelline affects the reaction [INS2 protein affects the expression of AGT protein]
oltipraz inhibits the reaction [trigonelline inhibits the reaction [Glucose results in increased expression of AGT mRNA]]; trigonelline inhibits the reaction [Glucose results in increased expression of AGT mRNA]		 CTD PMID:29211853 NCBI chr19:69,426,540...69,447,017
Ensembl chr19:52,529,185...52,540,977 		JBrowse link
G Atg7 autophagy related 7 multiple interactions ISO trigonelline inhibits the reaction [Palmitic Acid results in decreased expression of ATG7 protein]
ATG7 protein affects the reaction [trigonelline inhibits the reaction [Palmitic Acid results in increased expression of PPARG protein]]; ATG7 protein affects the reaction [trigonelline inhibits the reaction [Palmitic Acid results in increased expression of SREBF1 protein]]; trigonelline inhibits the reaction [Palmitic Acid results in decreased expression of ATG7 protein]		 CTD PMID:30208301 NCBI chr 4:149,390,000...149,597,534
Ensembl chr 4:147,718,752...147,925,593 		JBrowse link
G Bax BCL2 associated X, apoptosis regulator multiple interactions EXP
ISO		 trigonelline inhibits the reaction [[Oxygen deficiency co-treated with Glucose deficiency] results in increased expression of BAX protein]
[trigonelline co-treated with Cisplatin] results in increased expression of BAX protein; [trigonelline co-treated with Etoposide] results in increased expression of BAX protein		 CTD PMID:31935362 PMID:33148531 NCBI chr 1:105,076,472...105,081,906
Ensembl chr 1:95,938,808...95,945,368 		JBrowse link
G Bcl2 BCL2, apoptosis regulator multiple interactions EXP
ISO		 trigonelline inhibits the reaction [[Oxygen deficiency co-treated with Glucose deficiency] results in decreased expression of BCL2 protein]
[trigonelline co-treated with Cisplatin] results in decreased expression of BCL2 protein; [trigonelline co-treated with Etoposide] results in decreased expression of BCL2 protein		 CTD PMID:31935362 PMID:33148531 NCBI chr13:23,204,464...23,366,900
Ensembl chr13:22,684,989...22,853,743
Ensembl chr13:22,684,989...22,853,743 		JBrowse link
G Becn1 beclin 1 multiple interactions ISO trigonelline inhibits the reaction [Palmitic Acid results in decreased expression of BECN1 protein]
trigonelline inhibits the reaction [[Cholesterol, Dietary co-treated with Dietary Fats] results in decreased expression of BECN1 protein]; trigonelline inhibits the reaction [Palmitic Acid results in decreased expression of BECN1 protein]		 CTD PMID:30208301 NCBI chr10:86,731,649...86,747,002
Ensembl chr10:86,231,388...86,246,742 		JBrowse link
G Casp3 caspase 3 increases activity
multiple interactions		 ISO
EXP		 trigonelline results in increased activity of CASP3 protein
2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one inhibits the reaction [trigonelline inhibits the reaction [[Oxygen deficiency co-treated with Glucose deficiency] results in increased activity of CASP3 protein]]; trigonelline inhibits the reaction [[Oxygen deficiency co-treated with Glucose deficiency] results in increased activity of CASP3 protein]
[trigonelline co-treated with Cisplatin] results in increased cleavage of CASP3 protein; [trigonelline co-treated with Etoposide] results in increased cleavage of CASP3 protein		 CTD PMID:26593444 PMID:31935362 PMID:33148531 NCBI chr16:52,395,539...52,413,794
Ensembl chr16:45,662,910...45,684,648 		JBrowse link
G Cd36 CD36 molecule multiple interactions ISO trigonelline inhibits the reaction [[Cholesterol, Dietary co-treated with Dietary Fats] results in increased expression of CD36 protein]; trigonelline inhibits the reaction [Palmitic Acid results in increased expression of CD36 protein] CTD PMID:30208301 NCBI chr 4:18,209,088...18,302,142
Ensembl chr 4:17,354,466...17,513,903 		JBrowse link
G Ddit3 DNA-damage inducible transcript 3 multiple interactions ISO [trigonelline co-treated with ferric citrate] results in increased expression of DDIT3 mRNA CTD PMID:29959986 NCBI chr 7:65,001,695...65,006,517
Ensembl chr 7:63,116,380...63,121,201 		JBrowse link
G Egf epidermal growth factor multiple interactions ISO trigonelline inhibits the reaction [EGF protein results in increased phosphorylation of EGFR protein]; trigonelline inhibits the reaction [EGF protein results in increased phosphorylation of MAPK1 protein]; trigonelline inhibits the reaction [EGF protein results in increased phosphorylation of MAPK3 protein]; trigonelline inhibits the reaction [EGF protein results in increased phosphorylation of NFE2L2 protein] CTD PMID:33148531 NCBI chr 2:220,893,660...220,976,331
Ensembl chr 2:218,219,415...218,302,064 		JBrowse link
G Egfr epidermal growth factor receptor multiple interactions
decreases phosphorylation		 ISO trigonelline inhibits the reaction [EGF protein results in increased phosphorylation of EGFR protein]
trigonelline results in decreased phosphorylation of EGFR protein		 CTD PMID:33148531 NCBI chr14:95,378,626...95,551,358
Ensembl chr14:91,177,067...91,344,382 		JBrowse link
G Eif2s1 eukaryotic translation initiation factor 2 subunit alpha multiple interactions ISO trigonelline inhibits the reaction [Palmitic Acid results in increased phosphorylation of EIF2S1 protein] CTD PMID:30208301 NCBI chr 6:103,405,880...103,430,549
Ensembl chr 6:97,672,766...97,706,225 		JBrowse link
G Fth1 ferritin heavy chain 1 multiple interactions ISO [trigonelline co-treated with ferric citrate] results in increased expression of FTH1 mRNA CTD PMID:29959986 NCBI chr 1:216,052,037...216,054,325
Ensembl chr 1:206,627,103...206,725,424 		JBrowse link
G Ftl1 ferritin light chain 1 multiple interactions ISO [trigonelline co-treated with ferric citrate] results in increased expression of FTL mRNA CTD PMID:29959986 NCBI chr 1:105,072,858...105,074,705
Ensembl chr 1:95,936,387...95,939,725
Ensembl chr10:95,936,387...95,939,725
Ensembl chr 2:95,936,387...95,939,725 		JBrowse link
G Gclc glutamate-cysteine ligase, catalytic subunit multiple interactions ISO trigonelline inhibits the reaction [Pyocyanine results in increased expression of GCLC mRNA] CTD PMID:24015256 NCBI chr 8:87,510,251...87,548,896
Ensembl chr 8:78,630,127...78,668,544 		JBrowse link
G Hexb hexosaminidase subunit beta multiple interactions ISO trigonelline inhibits the reaction [iodixanol results in increased secretion of HEXB protein] CTD PMID:34774977 NCBI chr 2:30,218,608...30,238,771
Ensembl chr 2:28,484,012...28,504,223 		JBrowse link
G Hmox1 heme oxygenase 1 decreases expression ISO trigonelline results in decreased expression of HMOX1 mRNA; trigonelline results in decreased expression of HMOX1 protein CTD PMID:33148531 NCBI chr19:13,452,365...13,479,823
Ensembl chr19:13,467,244...13,474,079 		JBrowse link
G Hspa5 heat shock protein family A (Hsp70) member 5 multiple interactions ISO trigonelline inhibits the reaction [Palmitic Acid results in increased expression of HSPA5 protein] CTD PMID:30208301 NCBI chr 3:38,453,016...38,457,475
Ensembl chr 3:18,055,405...18,059,891 		JBrowse link
G Il1b interleukin 1 beta multiple interactions EXP trigonelline inhibits the reaction [[Oxygen deficiency co-treated with Glucose deficiency] results in increased expression of IL1B protein] CTD PMID:31935362 NCBI chr 3:137,030,200...137,036,581
Ensembl chr 3:116,577,010...116,583,415 		JBrowse link
G Il6 interleukin 6 multiple interactions EXP trigonelline inhibits the reaction [[Oxygen deficiency co-treated with Glucose deficiency] results in increased expression of IL6 protein] CTD PMID:31935362 NCBI chr 4:5,889,999...5,894,575
Ensembl chr 4:5,213,394...5,219,178 		JBrowse link
G Ins1 insulin 1 multiple interactions ISO trigonelline inhibits the reaction [[Cholesterol, Dietary co-treated with Dietary Fats] results in increased expression of INS1 protein] CTD PMID:30208301 NCBI chr 1:261,186,119...261,186,686
Ensembl chr 1:251,244,973...251,245,536 		JBrowse link
G Ins2 insulin 2 multiple interactions ISO oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of ACE mRNA]]; oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of ACE protein]]; oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of ACE2 mRNA]]; oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of ACE2 protein]]; oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of AGT mRNA]]; oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of AGT protein]]; oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of MAS1 mRNA]]; oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of MAS1 protein]]; oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of NFE2L2 protein]]; oltipraz inhibits the reaction [trigonelline affects the reaction [INS2 protein affects the expression of NFE2L2 mRNA]]; trigonelline affects the reaction [INS2 protein affects the expression of ACE mRNA]; trigonelline affects the reaction [INS2 protein affects the expression of ACE protein]; trigonelline affects the reaction [INS2 protein affects the expression of ACE2 mRNA]; trigonelline affects the reaction [INS2 protein affects the expression of ACE2 protein]; trigonelline affects the reaction [INS2 protein affects the expression of AGT mRNA]; trigonelline affects the reaction [INS2 protein affects the expression of AGT protein]; trigonelline affects the reaction [INS2 protein affects the expression of MAS1 mRNA]; trigonelline affects the reaction [INS2 protein affects the expression of MAS1 protein]; trigonelline affects the reaction [INS2 protein affects the expression of NFE2L2 mRNA]; trigonelline affects the reaction [INS2 protein affects the expression of NFE2L2 protein]; trigonelline inhibits the reaction [INS2 protein affects the abundance of angiotensin I (1-7)] CTD PMID:29211853 NCBI chr 1:207,272,738...207,421,998
Ensembl chr 1:197,843,281...197,864,775 		JBrowse link
G Keap1 Kelch-like ECH-associated protein 1 multiple interactions ISO [trigonelline co-treated with ferric citrate] results in decreased expression of KEAP1 mRNA CTD PMID:29959986 NCBI chr 8:28,044,555...28,054,042
Ensembl chr 8:19,768,375...19,777,862 		JBrowse link
G Lepr leptin receptor affects abundance ISO LEPR affects the abundance of trigonelline CTD PMID:20567778 NCBI chr 5:121,409,735...121,593,201
Ensembl chr 5:116,289,823...116,475,908 		JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions
decreases phosphorylation		 ISO trigonelline inhibits the reaction [EGF protein results in increased phosphorylation of MAPK1 protein]
trigonelline results in decreased phosphorylation of MAPK1 protein		 CTD PMID:33148531 NCBI chr11:97,462,025...97,529,193
Ensembl chr11:83,957,813...84,023,616 		JBrowse link
G Mapk3 mitogen activated protein kinase 3 multiple interactions
decreases phosphorylation		 ISO trigonelline inhibits the reaction [EGF protein results in increased phosphorylation of MAPK3 protein]
trigonelline results in decreased phosphorylation of MAPK3 protein		 CTD PMID:33148531 NCBI chr 1:190,797,189...190,803,411
Ensembl chr 1:181,366,637...181,372,863 		JBrowse link
G Mas1 MAS1 proto-oncogene, G protein-coupled receptor multiple interactions EXP
ISO		 oltipraz inhibits the reaction [trigonelline inhibits the reaction [Glucose results in decreased expression of MAS1 mRNA]]; trigonelline inhibits the reaction [Glucose results in decreased expression of MAS1 mRNA]
oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of MAS1 mRNA]]; oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of MAS1 protein]]; trigonelline affects the reaction [INS2 protein affects the expression of MAS1 mRNA]; trigonelline affects the reaction [INS2 protein affects the expression of MAS1 protein]		 CTD PMID:29211853 NCBI chr 1:50,428,064...50,459,537
Ensembl chr 1:47,880,309...47,911,709 		JBrowse link
G Mtor mechanistic target of rapamycin kinase multiple interactions ISO trigonelline inhibits the reaction [Palmitic Acid results in increased phosphorylation of MTOR protein] CTD PMID:30208301 NCBI chr 5:164,167,985...164,277,438
Ensembl chr 5:158,884,804...158,994,311 		JBrowse link
G Myc MYC proto-oncogene, bHLH transcription factor decreases expression ISO trigonelline results in decreased expression of MYC mRNA CTD PMID:26593444 NCBI chr 7:95,483,105...95,488,031
Ensembl chr 7:93,593,705...93,598,630 		JBrowse link
G Nfe2l2 NFE2 like bZIP transcription factor 2 multiple interactions
decreases phosphorylation		 ISO
EXP		 trigonelline inhibits the reaction [EGF protein results in increased phosphorylation of NFE2L2 protein]; trigonelline inhibits the reaction [ferric citrate affects the localization of NFE2L2 protein]; trigonelline inhibits the reaction [NFE2L2 protein results in decreased susceptibility to Cisplatin]; trigonelline inhibits the reaction [NFE2L2 protein results in decreased susceptibility to Etoposide]; trigonelline inhibits the reaction [Pyocyanine results in increased expression of and affects the localization of NFE2L2 protein]
trigonelline results in decreased phosphorylation of NFE2L2 protein
oltipraz inhibits the reaction [trigonelline inhibits the reaction [Glucose results in increased expression of NFE2L2 protein]]; trigonelline inhibits the reaction [Glucose results in increased expression of NFE2L2 protein]
oltipraz affects the reaction [trigonelline affects the reaction [INS2 protein affects the expression of NFE2L2 protein]]; oltipraz inhibits the reaction [trigonelline affects the reaction [INS2 protein affects the expression of NFE2L2 mRNA]]; trigonelline affects the reaction [INS2 protein affects the expression of NFE2L2 mRNA]; trigonelline affects the reaction [INS2 protein affects the expression of NFE2L2 protein]		 CTD PMID:24015256 PMID:29211853 PMID:29959986 PMID:33148531 NCBI chr 3:81,001,529...81,031,165
Ensembl chr 3:60,594,242...60,621,737 		JBrowse link
G Nqo1 NAD(P)H quinone dehydrogenase 1 multiple interactions
decreases expression		 ISO trigonelline inhibits the reaction [ferric citrate results in increased expression of NQO1 protein]; trigonelline inhibits the reaction [Pyocyanine results in increased expression of NQO1 mRNA]
trigonelline results in decreased expression of NQO1 mRNA; trigonelline results in decreased expression of NQO1 protein		 CTD PMID:24015256 PMID:29959986 PMID:33148531 NCBI chr19:52,205,374...52,220,267
Ensembl chr19:35,295,573...35,310,557 		JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 multiple interactions ISO trigonelline inhibits the reaction [Palmitic Acid results in increased cleavage of PARP1 protein]
[trigonelline co-treated with Cisplatin] results in increased cleavage of PARP1 protein; [trigonelline co-treated with Etoposide] results in increased cleavage of PARP1 protein		 CTD PMID:30208301 PMID:33148531 NCBI chr13:94,839,484...94,871,295
Ensembl chr13:92,307,586...92,339,404 		JBrowse link
G Plcg1 phospholipase C, gamma 1 multiple interactions ISO trigonelline inhibits the reaction [iodixanol results in increased phosphorylation of PLCG1 protein] CTD PMID:34774977 NCBI chr 3:169,805,299...169,836,040
Ensembl chr 3:149,385,587...149,416,330 		JBrowse link
G Plin1 perilipin 1 multiple interactions ISO trigonelline inhibits the reaction [Palmitic Acid results in increased expression of PLIN1 protein] CTD PMID:30208301 NCBI chr 1:133,664,294...133,676,854
Ensembl chr 1:133,664,892...133,676,828 		JBrowse link
G Pparg peroxisome proliferator-activated receptor gamma multiple interactions ISO ATG7 protein affects the reaction [trigonelline inhibits the reaction [Palmitic Acid results in increased expression of PPARG protein]]; trigonelline inhibits the reaction [Palmitic Acid results in increased expression of PPARG protein]
trigonelline inhibits the reaction [[Cholesterol, Dietary co-treated with Dietary Fats] results in increased expression of PPARG protein]; trigonelline inhibits the reaction [Palmitic Acid results in increased expression of PPARG protein]		 CTD PMID:30208301 NCBI chr 4:150,095,743...150,221,104
Ensembl chr 4:148,423,194...148,548,468 		JBrowse link
G Sqstm1 sequestosome 1 multiple interactions ISO trigonelline inhibits the reaction [[Cholesterol, Dietary co-treated with Dietary Fats] results in increased expression of SQSTM1 protein]; trigonelline inhibits the reaction [Palmitic Acid results in increased expression of SQSTM1 protein] CTD PMID:30208301 NCBI chr10:35,026,598...35,037,750
Ensembl chr10:34,525,519...34,536,673 		JBrowse link
G Srebf1 sterol regulatory element binding transcription factor 1 multiple interactions ISO trigonelline inhibits the reaction [[Cholesterol, Dietary co-treated with Dietary Fats] results in increased expression of SREBF1 protein]; trigonelline inhibits the reaction [Palmitic Acid results in increased expression of SREBF1 protein]
ATG7 protein affects the reaction [trigonelline inhibits the reaction [Palmitic Acid results in increased expression of SREBF1 protein]]; trigonelline inhibits the reaction [Palmitic Acid results in increased expression of SREBF1 protein]		 CTD PMID:30208301 NCBI chr10:45,507,152...45,529,164
Ensembl chr10:45,007,637...45,029,650 		JBrowse link
G Tnf tumor necrosis factor multiple interactions EXP 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one inhibits the reaction [trigonelline inhibits the reaction [[Oxygen deficiency co-treated with Glucose deficiency] results in increased expression of TNF protein]]; trigonelline inhibits the reaction [[Oxygen deficiency co-treated with Glucose deficiency] results in increased expression of TNF protein] CTD PMID:31935362 NCBI chr20:3,626,685...3,629,303
Ensembl chr20:3,622,011...3,624,629 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19899
    role 19870
      biological role 19868
        physiological role 19867
          food component 19867
            N-methylnicotinate 39
Path 2
Term Annotations click to browse term
  CHEBI ontology 19899
    subatomic particle 19897
      composite particle 19897
        hadron 19897
          baryon 19897
            nucleon 19897
              atomic nucleus 19897
                atom 19897
                  main group element atom 19836
                    main group molecular entity 19836
                      s-block molecular entity 19670
                        hydrogen molecular entity 19652
                          hydrides 19160
                            inorganic hydride 18179
                              pnictogen hydride 18169
                                nitrogen hydride 18082
                                  ammonium 8325
                                    ammonium ion derivative 8320
                                      quaternary ammonium ion 5301
                                        quaternary nitrogen compound 881
                                          iminium betaine 56
                                            N-methylnicotinate 39
paths to the root